Recent developments in palladium-catalyzed heterocycle synthesis and functionalization

Current Organic Chemistry

Volumn 9, Issue 7, 2005, Pages 625-655

  Wolfe, John P ^a   Thomas, Jennifer S ^b  

^a UNIVERSITY OF MICHIGAN   (United States)

^b LEBANON VALLEY COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYSIS; PALLADIUM;

BOND FORMING; CARBON CARBONS; CARBON-HETEROATOM BONDS; CYCLOADDITIONS; FUNCTIONALIZATIONS; HETEROCYCLE SYNTHESIS; PALLADIUM-CATALYZED; RING CLOSURES; SINGLE PROCESS;

SYNTHESIS (CHEMICAL);

CARBON; HETEROCYCLIC COMPOUND; PALLADIUM;

ALKYLATION; ALLYLATION; ANNULATION REACTION; ARYLATION; CATALYSIS; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CROSS COUPLING REACTION; CYCLIZATION; CYCLOADDITION; HECK REACTION; ORGANIC CHEMISTRY; REVIEW; RING CLOSING METATHESIS; SYNTHESIS;

EID: 17644364036     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272053764999     Document Type: Review

References (305)

1. Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry, Pergamon Press: Oxford, 2002.
2. Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century; John Wiley and Sons: New York, 2004.
3. Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3 4295-4298.
4. (a) Nakamura, I.; Yamamoto, Y. Chem Rev. 2004, 104, 2127-2198.
5. (b) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285-2309.
6. (c) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238.
7. (d) Barluenga, J.; Santamaria, J.; Tomas, M. Chem. Rev. 2004, 104, 2259-2283.
8. (e) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239-2258.
9. (f) Varela, J. A.; Saa, C. Chem. Rev. 2003, 103, 3787-3801.
10. (g) Rubin, M.; Sromek, A. W.; Gevorgyan, V. Synlett 2003, 2265-2291.
11. (h) Li, C.-L.; Liu, R.-S. Chem. Rev. 2000, 100 3127-3161.
12. (i) Yet, L. Chem. Rev. 2000, 100, 2963-3007.
13. (a) Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
14. (b) Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972, 37, 2320-2322.
15. (a) Link, J. T. Org. React. 2002, 60, 157-534.
16. (b) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003 103, 2945-2963.
17. (c) Dyker, G. in Handbook of Organopalladium Chemistry for Organic Synthesis Negishi, E.-i., Ed; John Wiley and Sons: Hoboken, 2002, vol 1, pp 1255-1282.
18. Dounay, A. B.; Hatanaka, K.; Kodanko, J. J.; Oestreich, M.; Overman, L. E.; Pfeifer, L. A.; Weiss, M. M. J. Am. Chem. Soc. 2003, 125, 6261-6271.
19. Overman, L. E.; Peterson, E. A. Angew. Chem. Int. Ed. 2003, 42, 2525-2528.
20. Kodanko, J. J.; Overman, L. E. Angew. Chem. Int. Ed. 2003, 42, 2528-2531.
21. Mori, M.; Nakanishi, M.; Kajishima, D.; Sato, Y. J. Am. Chem. Soc. 2003, 125, 9801-9807.
22. Lautens, M.; Fang, Y.-Q. Org. Lett. 2003, 5 3679-3682.
23. Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1990, 46, 4003-4018.
24. Watanabe, T.; Arai, S.; Nishida, A. Synlett 2004, 907-909.
25. Nazaré, M.; Schneider, C.; Lindenschmidt, A.; Will, D. W. Angew. Chem. Int. Ed. 2004, 43, 4526-4528.
26. (a) Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552-6554.
27. (b) Mori, K.; Rikimaru, K.; Kan, T.; Fukuyama, T. Org. Lett. 2004, 6, 3095-3097.
28. Gracias, V.; Moore, J. D.; Djuric, S. W. Tetrahedron Lett. 2004, 45, 417-420.
29. Xiang, Z.; Luo, T.; Lu, K.; Cui, J.; Shi, X.; Fathi, R.; Chen, J.; Yang, Z. Org. Lett. 2004, 6, 3155-3158.
30. Couty, S.; Liegault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511-2514.
31. Witulski, B.; Alayrac, C.; Tevzadze-Saeftel, L. Angew. Chem. Int. Ed. 2003, 42, 4257-4260.
32. (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1769.
33. (b) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047-1055.
34. (c) Dyker, G. Angew. Chem. Int. Ed. 1999, 38 1698-1712.
35. (d) Crabtree, R. H. J. Chem. Soc., Dalton Trans. 2001, 2437-2450.
36. Hennessy, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 12084-12085.
37. (a) Harayama, T.; Sato, T.; Hori, A.; Abe, H.; Takeuchi, Y. Synlett 2003, 1141-1144.
38. (b) Harayama, T.; Hori, A.; Abe, H.; Takeuchi, Y. Tetrahedron 2004, 60, 1611-1616.
39. (a) Campo, M. A.; Huang, Q.; Yao, T.; Tian, Q.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 11506-11507.
40. (b) Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 7460-7461.
41. Dppm = 1,1-bis(diphenylphosphino)methane
42. (a) Abbiati, G.; Beccalli, E. M.; Broggini, G.; Zoni, C. J. Org. Chem. 2003, 68, 7625-7628.
43. (b) Beccalli, E. M.; Broggini, G. Tetrahedron Lett. 2003, 44, 1919-1921.
44. Liu, C.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004 126, 10250-10251.
45. Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578-9579.
46. Pache, S.; Lautens, M. Org. Lett. 2003, 5, 4827-4830.
47. For a review on mechanistically related transformations, see: Catellani, M. Synlett 2003, 298-312.
48. For recent reviews, see: (a) Montgomery, J. Angew. Chem. Int. Ed. 2004, 43, 3890-3908.
49. (b) Fairlamb, I. J. S. Angew. Chem. Int. Ed. 2004 43, 1048-1052.
50. (c) Rubin, M.; Sromek, A. W.; Gevorgyan, V. Synlett 2003, 2265-2291.
51. (d) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215-236.
52. (e) Widenhoefer, R. A. Acc. Chem. Res. 2002, 35, 905-913.
53. (f) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16.
54. Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1985, 107, 1781-1783.
55. (a) Trost, B. M.; Chen, S.-F. J. Am. Chem. Soc. 1986 108, 6053-6054.
56. (b) Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42.
57. Aggarwal, V. K.; Butters, M.; Davies, P. W. Chem. Commun. 2003, 1046-1047.
58. (a) Trost, B. M.; Lee, D. C.; Rise, F. Tetrahedron Lett. 1989, 30, 651-654.
59. (b) Hatano, M.; Mikami, K. Org. Biomol. Chem. 2003 1, 3871-3873.
60. (c) Hatano, M.; Mikami, K. J. Am. Chem. Soc. 2003 125, 4704-4705.
61. Pei, T.; Widenhoefer, R. A. Org. Lett. 2000, 2 1469-1471.
62. Takacs, J. M.; Schroeder, S. D.; Hart, J.; Gifford, M.; Jiang, X.-T.; Saleh, T.; Vayalakkada, S.; Yap, A. H. Org. Lett. 2003, 5, 3595-3598.
63. Yamamoto, Y.; Kuwabara, S.; Ando, Y.; Nagata, H.; Nishiyama, H.; Itoh, K. J. Org. Chem. 2004, 69, 6697-6705.
64. (a) Kressierer, C. J.; Müller, T. J. J. Synlett 2004, 655-658.
65. (b) Kressierer, C. J.; Müller, T. J. J. Tetrahedron Lett. 2004, 45, 2155-2158.
66. (a) Ohno, H.; Miyamura, K.; Takeoka, Y.; Tanaka, T. Angew Chem. Int. Ed. 2003, 42, 2647-2650.
67. (b) Ohno, H.; Takeoka, Y.; Miyamura, K.; Kadoh, Y.; Tanaka, T. Org. Lett. 2003, 5, 4763-4766.
68. Cooper, I. R.; Grigg, R.; Hardie, M. J.; MacLachlan, W. S.; Sridharan, V.; Thomas, W. A. Tetrahedron Lett. 2003, 44 2283-2285.
69. Ph-Box = (2S,2′S)-4,4′-(1-methylethylidene)bis [2,5-dihydro-2-phenyl]oxazole
70. Ma, S.; Jiao, N.; Zheng, Z.; Ma, Z.; Lu, Z.; Ye, L.; Deng, Y.; Chen, G. Org. Lett. 2004, 6, 2193-2196.
71. For a recent review, see: Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2915.
72. Reppe, W.; Sweckendiek, W. J. Justus Liebigs Ann. Chem. 1948, 560, 104-116.
73. (a) Calvo, C.; Hosokawa, T.; Reinheimer, H.; Maitlis, P. M. J. Am. Chem. Soc. 1972, 94, 3237-3238.
74. (b) Maitlis, P. M. Pure Appl. Chem. 1973, 33 489-512.
75. Yamamoto, Y.; Nagata, A.; Nagata, H.; Ando, Y.; Arikawa, Y.; Tatsumi, K.; Itoh, K. Chem. Eur. J. 2003, 9, 2469-2483.
76. Sato, Y.; Tamura, T.; Mori, M. Angew. Chem. Int. Ed. 2004, 43, 2436-2440.
77. Semmelhack, M. F.; Chong, B. P.; Stauffer, R. D.; Rogerson, T. D.; Chong, A.; Jones, L. D. J. Am. Chem. Soc. 1975, 97 2507-2516.
78. Piers, E.; Marais, P. C. J. Org. Chem. 1990, 55, 3454-3455.
79. (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109.
80. (b) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370.
81. (c) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383.
82. (d) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234-245.
83. (a) Sole, D.; Vallverdu, L.; Solans, X.; Font-Bardia, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587-1594.
84. (b) Sole, D.; Diaba, F.; Bonjoch, J. J. Org. Chem. 2003, 68, 5746-5749.
85. (c) Bonjoch, J.; Diaba, F.; Puigbo, G.; Peidro, E.; Sole, D. Tetrahedron Lett. 2003, 44, 8387-8390.
86. (d) Sole, D.; Peidro, E.; Bonjoch, J. Org. Lett. 2000, 2, 2225-2228.
87. Shao, Z.; Chen, J.; Huang, R.; Wang, C.; Li, L.; Zhang, H. Synlett 2003, 2228-2230.
88. (a) Zhou, H.; Liao, X.; Cook, J. M. Org. Lett. 2004 6, 249-252.
89. (b) Zhao, S.; Liao, X.; Wang, T.; Flippen-Anderson, J.; Cook, J. M. J. Org. Chem. 2003, 68, 6279-6295.
90. (c) Yu, J.; Wang, T.; Liu, X.; Deschamps, J.; Flippen-Anderson, J.; Liao, X.; Cook, J. M. J. Org. Chem. 2003 68, 7565-7581.
91. Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66 3402-3415.
92. Bolm, C.; Okamura, H.; Verrucci, M. J. Organomet. Chem. 2003, 687, 444-450.
93. Dppb = 1,4-bis(diphenylphosphino)butane
94. Cook, G. R.; Sun, L. Org. Lett. 2004, 6, 2481-2484.
95. Boger, D. L.; Duff, S. R.; Panek, J. S.; Yasuda, M. J. Org. Chem. 1985, 50, 5782-5789.
96. (a) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem. Int. Ed. Engl. 1995, 34, 1348-1350.
97. (b) For related intermolecular reactions see: Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609-3612.
98. For recent reviews on Pd-catalyzed carbon-heteroatom bond-forming reactions, see: (a) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131-209.
99. (b) Hartwig, J. F. in Modern Arene Chemistry Astruc, D., Ed.; Wiley-VCH: Weinhem, Germany, 2002, pp 107-168.
100. (a) Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525-7546.
101. (b) Yang, B. H.; Buchwald, S. L. Org. Lett. 1999, 1, 35-37.
102. (c) Kuwabe, S.-i.; Torraca, K. E.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 12202-12206.
103. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553-5566.
104. Brain, C. T.; Steer, J. T. J. Org. Chem. 2003, 68, 6814-6816.
105. Evindar, G.; Batey, R. A. Org. Lett. 2003, 5 133-136.
106. (a) Cho, C. S.; Lim, D. K.; Heo, N. H.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2004, 104-105.
107. (b) Inamoto, K.; Katsuno, M.; Yoshino, T.; Suzuki, I.; Hiroya, K.; Sakamoto, T. Chem. Lett. 2004, 33, 1026-1027.
108. Dppp = 1,3-bis(diphenylphosphino)propane
109. Margolis, B. J.; Swidorski, J. J.; Rogers, B. N. J. Org. Chem. 2003, 68, 644-647.
110. Nozaki, K.; Takahashi, K.; Nakano, K.; Hiyama, T.; Tang, H.-Z.; Fujiki, M.; Yamaguchi, S.; Tamao, K. Angew. Chem. Int. Ed. 2003, 42, 2051-2053.
111. Schlapbach, A.; Heng, R.; Di Padova, F. Bioorg. Med. Chem. Lett. 2004, 14, 357-360.
112. Dppf = 1,1′-bis(diphenylphosphino)ferrocene
113. Nemoto, T.; Ohshima, T.; Shibasaki, M. Tetrahedron 2003, 59, 6889-6897.
114. Dpe-phos = bis(2-diphenylphosphinophenyl)ether
115. Kozawa, Y.; Mori, M. J. Org. Chem. 2003, 68 3064-3067.
116. Siebeneicher, H.; Bytschkov, I.; Doye, S. Angew. Chem. Int. Ed. 2003, 42, 3042-3044.
117. Xantphos = 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene
118. Manley, P. J.; Bilodeau, M. T. Org. Lett. 2004, 6, 2433-2435.
119. Harmata, M.; Hong, X. J. Am. Chem. Soc. 2003, 125, 5754-5756.
120. Cuny, G.; Bois-Choussy, M.; Zhu, J. Angew. Chem. Int. Ed. 2003, 42, 4774-4777.
121. Jonckers, T. H. M.; Maes, B. U. W.; Lemiere, G. L. F.; Rombouts, G.; Pieters, L.; Haemers, A.; Dommisse, R. A. Synlett 2003, 615-618.
122. Klapars, A.; Parris, S.; Anderson, K. W.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 3529-3533.
123. Phen = 1,10-phenanthroline
124. Smitrovich, J. H.; Davies, I. W. Org. Lett. 2004, 6, 533-535.
125. (a) Chiba, S.; Kitamura, M.; Saku, O.; Narasaka, K. B. Chem. Soc. Jpn. 2004, 77, 785-796.
126. (b) Zaman, S.; Kitamura, M.; Narasaka, K. B. Chem. Soc. Jpn. 2003, 76, 1055-1062.
127. (c) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45-46.
128. Helaja, J.; Göttlich, R. Chem. Commun. 2002, 720-721.
129. (a) Wolfe, J. P.; Rossi, M. A. J. Am. Chem. Soc. 2004, 126, 1620-1621.
130. (b) Ney, J. E.; Wolfe, J. P. Angew. Chem. Int. Ed. 2004, 43, 3605-3608.
131. (c) Lira, R.; Wolfe, J. P. J. Am. Chem. Soc. 2004 126, 13906-13907.
132. Dppe = 1,2-bis(diphenylphosphino)ethane
133. For recent reviews, see: (a) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079-3159.
134. (b) Roesky, P. W.; Müller, T. E. Angew. Chem. Int. Ed. 2003, 42, 2708-2710.
135. (c) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104-114.
136. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703.
137. (a) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673-686.
138. (b) Molander, G. A.; Romero, J. A. C. Chem. Rev. 2002, 102, 2161-2185.
139. (R,R)-RENORPHOS = (1R,2S,3R,4R -bicyclo[2.2.1]heptane-2,3-diylbis[diphenylphosphine]
140. Lutete, L. M.; Kadota, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 1622-1623.
141. Utimoto, K.; Miwa, H.; Nozaki, H. Tetrahedron Lett. 1981, 22, 4277-4278.
142. (a) van Esseveldt, B. C. J.; van Delft, F. L.; Smits, J. M. M.; de Gelder, R.; Schoemaker, H. E.; Rutjes, F. P. J. T. Adv. Synth. Catal. 2004, 346, 823-834.
143. (b) van Esseveldt, B. C. J.; van Delft, F. L.; de Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717-1720.
144. Utimoto, K. Pure Appl. Chem. 1983, 55, 1845-1852.
145. Mondal, S.; Nogami, T.; Asao, N.; Yamamoto, Y. J. Org. Chem. 2003, 68, 9496-9498.
146. Gabriele, B.; Salerno, G.; Fazio, A.; Pittelli, R. Tetrahedron 2003, 59, 6251-6259.
147. Qian, H.; Hart, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 9536-9537.
148. For a recent review, see: Hosokawa, T.; Murahashi, S.-I. in Handbook of Organopalladium Chemistry for Organic Synthesis Negishi, E.-i., Ed.; John Wiley and Sons: Hoboken, 2002, vol 2, pp 2141-2159.
149. Han, X.; Widenhoefer, R. A. J. Org. Chem. 2004, 69, 1738-1740.
150. Perlmutter, P.; Selajerern, W.; Vounatsos, F. Org. Biomol. Chem. 2004, 2, 2220-2228.
151. Hayashi, T.; Yamasaki, K.; Mimura, M.; Uozumi, Y. J. Am. Chem. Soc. 2004, 126, 3036-3037.
152. For a recent review, see: Stahl, S. S. Angew. Chem. Int. Ed. 2004, 43, 3400-3420.
153. (a) Fix, S. R.; Brice, J. L.; Stahl, S. S. Angew. Chem. Int. Ed. 2002, 41, 164-166.
154. (b) Trend, R. M.; Ramtohul, Y. K.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem. Int. Ed. 2003, 42, 2892-2895.
155. (c) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584-3585.
156. Miyazawa, M.; Hirose, Y.; Narantsetseg, M.; Yokoyama, H.; Yamaguchi, S.; Hirai, Y. Tetrahedron Lett. 2004, 45, 2883-2886.
157. (a) Ma, S.; Lu, L.; Zhang, J. J. Am. Chem. Soc. 2004 126, 9645-9660.
158. (b) Ma, S.; Zhang, J. Angew. Chem. Int. Ed. 2003, 42, 184-187.
159. Ma, S.; Zhang, J. J. Am. Chem. Soc. 2003, 125 12386-12387.
160. Balme, G.; Bouyssi, D.; Lomberget, T.; Monteiro, N. Synthesis 2003, 2115-2134.
161. Dai, G.; Larock, R. C. J. Org. Chem. 2003, 68 920-928.
162. Bossharth, E.; Desbordes, P.; Monteiro, N.; Bahne, G. Org. Lett. 2003, 5, 2441-2444.
163. Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Tetrahedron 2003, 59, 4661-4671.
164. Arcadi, A.; Cacchi, S.; Fabrizi, G.; Parisi, L. M. Tetrahedron Lett. 2004, 45, 2431-2434.
165. Huang, Q.; Larock, R. C. J. Org. Chem. 2003, 68, 980-988.
166. Ma, S.; Yu, Z. Angew. Chem. Int. Ed. 2003, 42 1955-1957.
167. (a) Ma, S.; Li, L. Org. Lett. 2000, 2, 941-944.
168. (b) Ma, S.; Gao, W. J. Org. Chem. 2002, 67, 6104-6112.
169. (c) Ma, S.; Yu, F.; Gao, W. J. Org. Chem. 2003, 68, 5943-5949.
170. (d) Ma, S. Acc. Chem. Res. 2003, 36, 701-712.
171. (a) Kamijo, S.; Yamamoto, Y. J. Org. Chem. 2003, 68, 4764-4771.
172. (b) Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2002 124, 11940-11945.
173. Verboom, R. C.; Persson, B. A.; Backvall, J. E. J. Org. Chem. 2004, 69, 3102-3111.
174. (a) Ohno, H.; Hamaguchi, H.; Ohata, M.; Kosaka, S.; Tanaka, T. J. Am. Chem. Soc. 2004, 126, 8744-8754.
175. (b) Ohno, H.; Hamaguchi, H.; Ohata, M.; Tanaka, T. Angew. Chem. Int. Ed. 2003, 42, 1749-1753.
176. Lei, A.; Lu, X.; Liu, G. Tetrahedron Lett. 2004, 45, 1785-1788.
177. For recent reviews, see: (a) Tsjui, J. in Handbook of Organopalladium Chemistry for Organic Synthesis Negishi, E.-i., Ed.; John Wiley and Sons: Hoboken, 2002, vol 2, pp 1669-1687.
178. (b) Acemoglu, L.; Williams, J. M. J. in Handbook of Organopalladium Chemistry for Organic Synthesis Negishi, E.-i:, Ed.; John Wiley and Sons: Hoboken, 2002, vol 1, pp 1689-1705.
179. Trost, B. M.; Shen, H. C.; Surivet, J.-P. Angew. Chem. Int. Ed. 2003, 42, 3943-3947.
180. (R,R)-Trost Ligand = (1R,2R)-N,N pm-bis(2′-diphenylphosphino-benzoyl)-1,2-diaminocyclohexane
181. Lucas, B. S.; Burke, S. D. Org. Lett. 2003, 5 3915-3918.
182. Ferber, B.; Lemaire, S.; Mader, M. M.; Prestat, G.; Poli, G. Tetrahedron Lett. 2003, 44, 4213-4216.
183. (a) Trost, B. M.; Fandrick, D. R. J. Am. Chem. Soc. 2003, 125, 11836-11837.
184. (b) Zhou, H. B.; Alper, H. J. Org. Chem. 2003, 68, 3439-3445.
185. (c) Zhou, H. B.; Alper, H. Tetrahedron 2004, 60, 73-79.
186. (a) Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1979, 101, 6429-6432.
187. (b) Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1979, 101, 6432-6433.
188. For recent reviews, see: (a) Chan, D. M. T in Cycloaddition Reactions in Organic Synthesis, Kobayashi, S.; Jorgensen, K. A., eds., Wiley-VCH: Weinheim, Germany, 2002, pp 57-84.
189. (b) Ogoshi, S. in Handbook of Organopalladium Chemistry for Organic Synthesis Negishi, E.-i., Ed; John Wiley and Sons: Hoboken, 2002, vol 2, pp 1995-2009.
190. (a) Jones, M. D.; Kemmitt, R. D. W. Chem. Commun. 1986, 1201-1203.
191. (b) Trost, B. M.; King, S. A.; Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902-5915.
192. (c) Trost, B. M.; Marrs, C. M.; J. Am. Chem. Soc. 1993, 115, 6636-6645.
193. Bambal, R. B.; Kemmitt, R. D. W. J. Orgonomet. Chem. 1989, 362, C18-C20.
194. (a) Hedley, S. J.; Moran, W. J.; Price, D. A.; Harrity, J. P. A. J. Org. Chem. 2003, 68, 4286-4292.
195. (b) Moran, W. J.; Goodenough, K. M.; Raubo, P.; Harrity, J. P. A. Org. Lett. 2003, 5, 3427-3429.
196. (a) Delgado, A.; Rodriguez, J. R.; Castedo, L.; Mascarenas, J. L. J. Am. Chem. Soc. 2003, 125, 9282-9283.
197. (b) Siriwardana, A. I.; Nakamura, I.; Yamamoto, Y. J. Org. Chem. 2004, 69, 3202-3204.
198. (c) Oh, B. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Heterocycles 2003, 61, 247-257.
199. (a) Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 7786-7787.
200. (b) Kamijo, S.; Jin, T.; Yamamoto, Y. Tetrahedron Lett. 2004, 45, 689-691.
201. (c) Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Org. Chem. 2004, 69, 2386-2393.
202. For recent reviews, see: (a) Larock, R. C. J. Organomet. Chem. 1999, 576, 111-124.
203. (b) Cacchi, S.; Fabrizi, G.; Goggiomani, A. Heterocycles 2002, 56, 613-632.
204. (c) Cacchi, S. J. Organomet. Chem. 1999, 576 42-64.
205. Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690.
206. Gathergood, N.; Scammells, P. J. Org. Lett. 2003, 5, 921-923.
207. (a) Kadnikov, D. V.; Larock, R. C. J. Org. Chem. 2003, 68, 9423-9432.
208. (b) Kadnikov, D. V.; Larock, R. C. J. Org. Chem. 2004, 69, 6772-6780.
209. (a) Zhang, H.; Larock, R. C. Org. Lett. 2001, 3, 3083-3086.
210. (b) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002 67, 86-94.
211. (c) Zhang, H.; Larock, R. C. J. Org. Chem. 2003, 68, 5132-5138.
212. Magnus, P.; Matthews, K. S.; Lynch, V. Org. Lett. 2003, 5, 2181-2184.
213. Huang, Q.; Larock, R. C. J. Org. Chem. 2003, 68, 7342-7349.
214. (a) Rozhkov, R. V.; Larock, R. C. Org. Lett. 2003 5, 797-800.
215. (b) Rozhkov, R. V.; Larock, R. C. J. Org. Chem. 2003 68, 6314-6320.
216. Rozhkov, R. V.; Larock, R. C. Tetrahedron Lett. 2004 45, 911-914.
217. Trost, B. M.; Toste, F. D.; Greenman, K. J. Am. Chem. Soc. 2003, 125, 4518-4526.
218. (a) Kitamura, T.; Yamamoto, K.; Kotani, M.; Oyamada, J.; Jia, C.; Fujiwara, Y. B. Chem. Soc. Jpn. 2003, 76, 1889-1895.
219. (b) Kotani, M.; Yamamoto, K.; Oyamada, J.; Fujiwara, Y.; Kitamura, T. Synthesis 2004, 1466-1470.
220. For recent reviews, see: Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101-4111 and references cited therein.
221. Szlosek-Pinaud, M.; Diaz, P.; Martinez, J.; Lamaty, F. Tetrahedron Lett. 2003, 44, 8657-8659.
222. (a) Dhawan, R.; Arndtsen, B. A. J. Am. Chem. Soc. 2004, 126, 468-469.
223. (b) Dhawan, R.; Dghaym, R. D.; Arndtsen, B. A. J. Am. Chem. Soc. 2003, 125, 1474-1475.
224. (a) Clique, B.; Vassiliou, S.; Monteiro, N.; Balme, G. Eur. J. Org. Chem. 2002, 1493-1499.
225. (b) Clique, B.; Anselme, C.; Otto, D.; Monteiro, N.; Balme, G. Tetrahedron Lett. 2004, 45, 1195-1197.
226. (c) Azoulay, S.; Monteiro, N.; Balme, G. Tetrahedron Lett. 2002, 43, 9311-9314.
227. (a) Gai, X.; Grigg, R.; Khamnaen, T.; Rajviroongit, S.; Sridharan, V.; Zhang, L.; Collard, S.; Keep, A. Tetrahedron Lett. 2003, 44, 7441-7443.
228. (b) Gai, X.; Grigg, R.; Koppen, I.; Marchbank, J.; Sridharan, V. Tetrahedron Lett. 2003, 44, 7445-7448.
229. Karpov, A. S.; Oeser, T.; Müller, T. J. J. Chem. Commun. 2004, 1502-1503.
230. For recent reviews, see: (a) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077-1101.
231. (b) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1470.
232. Farina, V.; Krishnanmurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
233. Suzuki, A. in Modern Arene Chemistry Astruc, D., Ed.; Wiley-VCH: Weinhem, Germany, 2002, pp 53-106.
234. Negishi, E.-i. in Handbook of Organopalladium Chemistry for Organic Synthesis Negishi, E.-i., Ed.; John Wiley and Sons: Hoboken, 2002, vol 1, pp 229-247.
235. (a) Denmark, S. E.; Sweis, R. F. Chem. Pharm. Bull. 2002, 50, 1531-1541.
236. (b) Hiyama, T. in Metal-Catalyzed Cross-Coupling Reactions Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany; 1998, pp 421-453.
237. Sonogashira, K. J. Organomet. Chem. 2002, 653 46-49.
238. For recent reviews, see: (a) Undheim, K. in Handbook of Organopalladium Chemistry for Organic Synthesis Negishi, E.-i., Ed.; John Wiley and Sons: Hoboken, 2002, vol 1, pp 409-492.
239. (b) Undheim, K.; Benneche, T. Adv. Heterocycl. Chem. 1995, 62, 305-418.
240. For a recent review on Suzuki coupling of heteroaryl boronic acids, see: Tyrrell, E.; Brookes, P. Synthesis 2003, 469-483.
241. (a) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem. Int. Ed. 2004, 43, 1871-1876.
242. (b) Barder, T. E.; Buchwald, S. L. Org. Lett. 2004 6, 2649-2652.
243. Zapf, A.; Jackstell, R.; Rataboul, F.; Reirmeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38-39.
244. Feuerstein, M.; Doucet, H.; Santelli, M. J. Organomet. Chem. 2003, 687, 327-336.
245. Denmark, S. E.; Baird, J. D.; Org. Lett. 2004, 6, 3649-3652.
246. Corley, E. G.; Conrad, K.; Murry, J. A.; Savarin, C.; Holko, J.; Boice, G. J. Org. Chem. 2004, 69, 5120-5123.
247. Albaneze-Walker, J.; Bazaral, C.; Leavey, T.; Dormer, P. G.; Murry, J. A. Org. Lett. 2004, 6, 2097-2100.
248. Kumar, K.; Zapf, A.; Michalik, D.; Tillack, A.; Heinrich, T.; Böttcher, H.; Arlt, M.; Beller, M. Org. Lett. 2004, 6 7-10.
249. (a) Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191-4194.
250. (b) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691-1694.
251. (c) Ma, Y.; Song, C.; Jiang, W.; Wu, Q.; Wang, Y.; Liu, X.; Andrus, M. B. Org. Lett. 2003, 5, 3317-3319.
252. (d) Park, S. B.; Alper, H. Chem. Commun. 2004, 1306-1307.
253. (e) Gelman, D.; Buchwald, S. L. Angew. Chem. Int. Ed. 2003, 42, 5993-5996.
254. (f) Arques, A.; Aunon, D.; Molina, P. Tetrahedron Lett. 2004, 45, 4337-4340.
255. (g) Cheng, J.; Sun, Y.; Wang, F.; Guo, M.; Xu, J.-H.; Pan, Y.; Zhang, Z. J. Org. Chem. 2004, 69, 5428-5432.
256. (h) Alonso, D. A.; Najera, C.; Pacheco, M. C. Adv. Synth. Catal. 2003, 345, 1146-1158.
257. CuTc = Copper 2-thiophenecarboxylate
258. Libeskind, L. S.; Srogl, J. Org. Lett. 2002, 4 979-981.
259. Lengar, A.; Kappe, C. O. Org. Lett. 2004, 6 771-774.
260. Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240-7241.
261. Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158-1174.
262. Rataboul, F.; Zapf, A.; Jackstell, R.; Harkal, S.; Riermeier, T.; Monsees, A.; Dingerdissen, U.; Beller, M. Chem. Eur. J. 2004 10, 2983-2990.
263. Hooper, M. W.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2003, 68, 2861-2873 and references cited therein.
264. Michalik, D.; Kumar, K.; Zapf, A.; Tillack, A.; Arlt, M.; Heinrich, T.; Beller, M. Tetrahedron Lett. 2004, 45, 2057-2061.
265. Lakshman, M. K.; Gunda, P. Org. Lett. 2003, 5 39-42.
266. (a) Enguehard, C.; Allouchi, H.; Gueiffier, A.; Buchwald, S. L. J. Org. Chem. 2003, 68, 4367-4370.
267. (b) Ferreira, I. C. F. R.; Queiroz, M.-J. R. P.; Kirsch, G. Tetrahedron 2003, 59, 975-981.
268. (c) Castellote, I.; Vaquero, J. J.; Alvarez-Builla, J. Tetrahedron Lett. 2004, 45, 769-772.
269. For recent mechanistic studies on catalytic aminations of heteroaromatic halides, see: Hooper, M. W.; Hartwig, J. F. Organometallics 2003, 22, 3394-3403.
270. Alcaraz, L.; Bennion, C.; Morris, J.; Meghani, P.; Thom, S. M. Org. Lett. 2004, 6, 2705-2708.
271. (a) Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423-1426.
272. (b) Viciu, M. S.; Germaneau, R. F.; Navarro-Fernandez, O.; Stevens, E. D.; Nolan, S. P. Organometallics 2002, 21, 5470-5472.
273. (a) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003 5, 793-796.
274. (b) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581-584.
275. (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727-7729.
276. (b) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
277. Steinhuebel, D.; Palucki, M.; Askin, D.; Dolling, U. Tetrahedron Lett. 2004, 45, 3305-3307.
278. Li, C. S.; Dixon, D. D. Tetrahedron Lett. 2004, 45, 4257-4260.
279. (a) Wolter, M.; Nordmann, G.; Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 973-976.
280. (b)Torraca, K. E.; Huang, X.; Parrish, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 10770-10771.
281. (a) Comely, A. C.; Eelkema, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 8714-8715.
282. (b) Babu, R. S.; O'Doherty, G. A. J. Am. Chem. Soc. 2003, 125, 12406-12407.
283. (c) Kim, H.; Men, H.; Lee, C. J. Am. Chem. Soc. 2004 126, 1336-1337.
284. (a) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernandez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827-828.
285. (b) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580.
286. Old, D. W.; Harris, M. C.; Buchwald, S. L. Org. Lett. 2000, 2, 1403-1406.
287. (a) Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578-5587.
288. (b) Enguehard, C.; Allouchi, H.; Gueiffier, A.; Buchwald, S. L. J. Org. Chem. 2003, 68, 5614-5617.
289. (c) Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684-11688.
290. Collmann, J. P.; Zhong, M. Org. Lett. 2000, 2 1233-1236.
291. For examples of stoichiometric copper-mediated processes see: (a) Chan, D. M. T.; Monaco, K. L.; Li, R.; Bonne, D.; Clark, C. G.; Lam, P. Y. S. Tetrahedron Lett. 2003, 44, 3863-3865.
292. (b) Bakkestuen, A. K.; Gundersen, L.-L. Tetrahedron Lett. 2003, 44, 3359-3362 and references cited therein.
293. Akita, Y.; Itagaki, Y.; Takizawa, S.; Ohta, A. Chem. Pharm. Bull. 1989, 37, 1477-1480.
294. For a recent review, see: Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 211-241.
295. (a) Yokooji, A.; Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2003, 59, 5685-5689.
296. (b) Mori, A.; Sekiguchi, A.; Masui, K.; Shimada, T.; Horie, M.; Osakada, K.; Kawamoto, M.; Ikeda, T. J. Am. Chem. Soc. 2003 125, 1700-1701.
297. (c) Park, C.-H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159-1162.
298. (d) Glover, B.; Harvey, K. A.; Liu, B.; Sharp, M. J.; Tymoschenko, M. F. Org. Lett. 2003, 5, 301-304.
299. (a) Lane, B. S.; Sames, D. Org. Lett. 2004, 6 2897-2900.
300. (b) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003, 125, 5274-5275.
301. (c) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003, 125, 10580-10585.
302. For an example of cobalt catalyzed arylation of thiazole, see: Sezen, B.; Sames, D. Org. Lett. 2003, 5, 3607-3610.
303. Masui, K.; Ikegami, H.; Mori, A. J. Am. Chem. Soc. 2004, 126, 5074-5075.
304. (a) Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300-2301.
305. (b) Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542-9543.